


Takeoff

by CeliPuff



Series: Love at First Flight [2]
Category: Supernatural
Genre: Bisexual Dean Winchester, Bottom Benny Lafitte, Bottom Castiel/Top Dean Winchester, Castiel and Dean Winchester Have a Profound Bond, Castiel is Not Innocent (Supernatural), Castiel/Dean Winchester First Date, Dean Winchester Has a Crush on Castiel, Dean Winchester Has a Panty Kink, Everyone Is Gay, Happy Ending, M/M, Openly Gay Castiel (Supernatural), POV Dean Winchester, Pride Parades, Public Sex, Shameless Smut, Sorry Not Sorry, They Forget About Benny, Threesome, Threesome - M/M/M, Top Castiel
Language: English
Status: Completed
Published: 2020-04-02
Updated: 2020-04-15
Packaged: 2021-02-28 18:14:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 6,257
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23441524
Author URL: https://archiveofourown.org/users/CeliPuff/pseuds/CeliPuff
Summary: Although Dean can’t seem to shake the blue eyed one night stand from his mind, he still never expected to see him again.Especially when being invited for a spontaneous threesome.Guess you can’t ignore fate...
Relationships: Castiel/Benny Lafitte/Dean Winchester, Castiel/Dean Winchester
Series: Love at First Flight [2]
Series URL: https://archiveofourown.org/series/1686745
Comments: 28
Kudos: 156





	1. Chapter 1

**Author's Note:**

> Part two is here and I’m almost sorry for it... almost. 
> 
> This fic was motivated by a fic called Cajun Heat by Ketch22, who was also my beta. 
> 
> Enjoy the smut!

So normally, Dean has a one night stand, it’s either good or bad, rarely mind blowing but hey, it happens. What isn’t normal, is Dean becoming hooked after _one_ hookup. 

Cas was… _awesome._ Dean’s tried to think of more profound words, but none cut it, he’s fucking awesome. Or he was awesome. _Was._ Because Dean would never see him again. Which was the point of him using a dating app _at_ the damn airport. Bathroom quicky, blow off some steam before a flight, move on with your life. Except, he couldn’t. 

He was mostly fine with it, I mean, there was nothing he could do about it so he had to be. Charlie called him out, saying a quick fuck was supposed to keep him from being a grouch, not the other way around and she was right. He got some release, the dude was… _gorgeous,_ he should focus on the positive things. 

She let him mope the first night. They ate shitty Chinese food and watched the Lord of the Rings Trilogy, even argued over who was hotter. _Spoiler alert; Dean was officially a sucker for blue eyes._ But none of those eyes compared to Cas’. 

Day two was sightseeing and the Pride Parade. After a while, Dean found himself actually enjoying it. It took a few drinks, but he finally loosened up and started talking to a man named Benny. He was hot, no doubting that. He also had blue eyes, dark hair, _yeah yeah, don't judge,_ and the conversation was fun. _Why not?_ Oh, and let’s not forget his southern drawl.

They got hammered and walked back to his place, stumbling inside and heatedly making out but Dean suddenly realized they hadn’t discussed what exactly was going on here because Dean did _not_ bottom. He planned on trying it one day but not until he was in an actual relationship with someone, not some random hookup. He broke the kiss, “I’m a top… we didn’t clarify that.” Rubbing the back of his neck, Dean waited for the rejection. Benny definitely gave top vibes now that Dean was thinking about it.

“Not a problem here Cher, I’m a switch.” Benny shrugged and took off his shirt.

“Switch?” Dean was still new to all this.

Benny huffed a laugh, “I like both top and bottom. I prefer to top but if the man knows what he’s doing, I’m all for it.”

Dean face shrugged, “Alright.” And then pulled off his own shirt.

**********

If Dean pictured Castiel while he fucked Benny, that was his own business.

The sex was great and they actually exchanged phone numbers this time. It was an awkward, _we’re obviously not looking for anything more than this but I’m in town until Monday,_ conversation but Benny looked happy to have a way to contact Dean before they went their separate ways. 

He couldn’t figure out why he was still thinking of Cas. They spent all of thirty minutes together, _total._

“So… you’re still thinking of that airport ass huh?” Charlie asked, once they found eachother in the confusing San Francisco streets. 

“Nah.” _Yes._

“Whatever you say, Dean. But you’ve always been a hopeless romantic.” 

“Shut up, Chuckles.” But he smiled along with his eye roll.

**********

Sunday, Dean got a text from Benny.

**Benny: Hey Cher. How about some** **_Cajun Heat_ ** **before you leave town?**

**Dean: Sounds awesome**

**Benny: Got any plans tonight?**

**Dean: Not really, my little sister would understand**

**Benny: You think three’s a crowd?**

Staring at his phone with his eyes wide, Dean blushed, even though Benny couldn’t see him.

“Dean, are you blushing??” Charlie asked in a confused tone.

“Uh… that guy from Pride just texted.” He was still grinning.

“Just don’t get in trouble and call if you need a ride.” She laughed and shook her head.

“No no… well yeah, but he just asked if I’m down for a threesome.” He set his phone aside.

“We both know you’re going. So, why are you still talking to me?” She teased.

“I just didn’t expect it.”

“Do you not want it?” She asked, confused as to why he even hesitated.

“Yeah, actually. I was looking for an experience and I’d definitely be getting that.” _So, why am I still thinking about Cas?_

“Just go. You’ll regret it if you don’t.” Charlie was right on that one, so he responded.

**Dean: I’m on the way**

**********

Dean was a little too eager and left Charlie’s studio before he even knew where he was going. All these damn streets looked alike, not to mention he was pretty hammered that night. Benny ended up picking him up and driving him to his apartment, which was actually only a few blocks from Charlie’s and it made Dean feel better, if things got too awkward, he could definitely walk back.

They got to Benny’s place and sat on the couch for a beer. “James should be here soon, I think you two will get along nicely. He’s a little bratty sometimes but ain’t nothing a little spankin can’t fix, right brotha?” He held out his beer and Dean found himself cheering to that a little too excitedly. 

“What’s he look like?” Dean asked, hoping to see a photo first.

Benny huffed a laugh, “I’m not showing you, that’s a surprise.” He took a drink of his beer, “But he’s pretty. Dark hair, blue eyes, but not like me, he’s much prettier with a nice fat cock. One of the only few others that I’ve bottomed for and actually enjoyed it.” 

Dean smiled, “Am I one of those dudes?”

“Think you’d be here otherwise? I only get my pretty, blue eyed fuck buddy once or twice a year and I damn sure have never shared him, but I don’t know, I think all three of us need this if that makes sense. I know you’re a hard top, that won't be an issue. I’ll bottom for him, he’ll bottom for you, he’ll be a good middle, trust me.” Dean listened to Benny like they were discussing some arbitrary business arrangement. “He mentioned wanting to take us both at the same time but I honestly don’t know if that is possible, we’d probably split him open.” And _that_ made Dean’s cock twitch. He’d never considered doing that before but apparently his dick was making the decisions here tonight. 

“Fuck. I’m going to go use the bathroom and marinate on what the hell you just said.” Dean stood and set his beer on the table. 

“Don’t jack off in there now.” Benny teased as his phone began to vibrate. While in the bathroom, he heard Benny leave his apartment and return a few moments later, surely with this _James_ in tow. 

_Alright Dean, get your game face on. Don’t make a fool of yourself, just act like you belong._ Dean’s usual pep talk got him to finally exit the bathroom. He could see _James,_ from behind and had to double take, he really looked like…

He turned around and their eyes locked, both completely frozen. “Cas??” What were the fucking odds? Like one in a billion? Was this some cosmic joke? He stepped closer like his face would change.

“Is this some kind of joke?” Cas asked and yup, that was definitely Mr. Phone Sex, because his voice went straight to Dean’s dick.

Benny was confused, “Ya’ll know each other?”

Cas stared at Benny like he was trying to read him. “You can say that, was this not planned?” He turned back at Dean like maybe his face had answers, but Dean probably looked like a clueless idiot. 

“Um, no, how the hell could we have planned this?” Dean asked. Even in all this confusion, he still had a semi.

“Dean, what did you call him?” Benny asked, like he just remembered they used different names.

Cas actually blushed and spoke up, “Oh about that, my name isn’t James, it’s Castiel.”

Benny looked more offended by this information than anything else, “And you asked if _I_ was pulling some kinda joke? We’ve been fucking for three years Ja— _Cas.”_

“Look, I never give out my real name, I didn’t expect to ever see you again and then by the fourth time we fucked it just felt weird saying I lied about my name.” Cas ran a hand through his hair. “James is my middle name, if that helps.” 

“Hell naw it doesn’t. But that mouth can make up for it.” Dean felt a little hopeful after Benny said that, like maybe this was still on. “Whatever your name is, I still can’t find someone with a mouth even remotely close to yours.” 

Dean pushed away the pang of jealousy he felt, but he definitely felt it. He still hadn’t felt those beautiful lips on his cock. 

“My name is Cas.” He glanced back over at Dean. “I’m still down, if you are.” 

“Wait, and how did y'all meet? At Pride too?” Benny asked, palming the semi he had as well.

Dean shook his head and found his voice, “No actually, we met at an airport.” 

“And he told _you_ his real name? Ain’t that abouta bitch?” He didn’t sound angry, but his feelings were undoubtedly wounded. 

Dean just shrugged, _why did Cas tell him his real name and not the dude he’s fucked numerous amounts of time? Weird… or maybe Cas felt the connection too?_ Now wasn’t the time to think about that though, because Cas had taken a few steps towards Dean. “Sorry Benny, I’ll make it up to you but Dean here needs me more right now, don’t you?” He tilted his head and pulled off his shirt, then began on his pants. Their eyes were still locked and Dean nodded without even realizing. _Yes Cas, I’ve needed you for days._

To Dean’s surprise, Cas stepped out of his chucks and dropped his jeans, revealing the hottest thing Dean had _ever_ seen. Castiel was wearing a blue thong. “Like what you see, baby?” His voice was as deep as a baritone now and Dean’s semi had graduated in seconds. He reached him then, and began lifting Dean’s shirt. It was much too easy to forget Benny was there but when Dean heard his pants fall against the hardwood floor he looked over, the spell broken. 

“Don’t mine me Cher, go on now.” He nodded towards Cas and pulled off his boxers, gripping his cock like he was loving the show. 

Dean complied and when he turned back towards Cas, he had already taken his shirt off and was shoving down his pants and boxers in one go. “Shoes off.” Cas ordered, and Dean quickly did as told, his breath catching in his throat as Cas dropped to his knees and began kissing up Dean’s thighs. “I get to take my time with you, tonight.” He growled, just before sliding his tongue up Dean’s cock and swirling it around the head, lapping up his precome. 

Dean tried to hide the chill up his spine but he felt Cas smile around his cock. He motioned for Benny to join and then turned, sliding his cock inside his mouth while stroking Dean. This was just too fucking hot. Dean was torn between not wanting to share Cas _and_ wanting to watch Benny wreck his ass while Cas sucked his cock. It was easy to see why Benny said Cas would be a good middle. He treated both their cocks like they were the only one, giving them equal attention and after a bit, he pulled them closer so he could suck both at once. They couldn’t get deep, or feel much more than wet heat, but it was still the hottest thing Dean had ever seen. He was slightly disappointed when Benny pulled him in for a kiss. He didn’t want to look away from Cas.

All too soon, Cas was pulling off and standing, walking towards Benny’s bedroom and leaving them behind. They smirked at each other and followed, surely looking like horny hounds following the scent of heat.

And in a way, they were.

Castiel presented himself on the bed in a way that was so inviting, it took all of Dean’s resolve not to push Benny aside and take Cas all to himself. “Dean…” Cas licked his lips. “What hole you want first, baby?” 

He reached back and pulled out a plug, tossing it on the floor and Dean fell even more in love with the damn panties. He could see everything important and yet still would have some panties to grip while he fucked into him, “Ass.” He said before looking at Benny, he nodded and walked around towards Cas’ front. 

Dean couldn’t focus on what was going on up there, not yet at least but he was thankful when Benny tossed him a condom and bottle of lube. They attempted a condom last time, before it shredded to hell, but hopefully _this_ condom held up. He slid a couple fingers inside, thankful the plug had started this job already because he needed to be inside Cas like yesterday. 

He glanced up while fingering Cas and saw Benny had pulled out a plug as well and was sprawled out in front with his cock already in Cas’ mouth, it looked like Cas was also working Benny open but Dean couldn’t see much. He slid out his fingers and quickly slid inside, groaning at his tight welcoming channel. “Fuck Casss…” 

Cas moaned and pushed back, his mouth still around Benny’s cock. Dean reached around and stroked Cas while he slowly rocked into him. _What was it about this guy that had Dean completely unglued?_ He was inside of him and _still_ wanted more. Dean started kissing and sucking along Cas’ back, still stroking him. 

He felt the bed shift and sat up in time to see Cas sitting up and Benny flipping around in front of him, presenting himself to Cas while he slid a condom on. “Push in deep Dean and hold it while I get inside this grizzly bear.” Dean huffed a laugh and pushed inside, peering around Cas so he could watch as he slid inside Benny. 

Okay, _this_ was the hottest thing ever. As was everything Cas did. 

Dean and Benny both stayed mostly still as Cas worked them both, pushing back into Dean and fucking up into Benny. This was like porn, but a million times better and Dean never imagined it could be so good, Cas was the ultimate wet dream. 

They knew they wouldn’t _both_ fit inside of Cas’ ass and that was okay, because _this_ was heaven. 

Cas gripped Benny’s hips but turned his face so he and Dean could make out. They moaned into each other’s mouth as they got closer and closer to the edge but were interrupted by Benny asking Cas to pause so he could take a piss.

_Pause._ There was no pausing this. The second he left the room Cas was shoving Dean backwards and straddling his lap, sliding down in one swift movement and riding Dean like it was the last thing he would ever do. 

Cas was close, and he didn’t give a damn if Benny missed out, and for some reason, that turned Dean on even more, if that were even possible. He reached and gripped Cas’ slick cock and pulled off the condom to jerk him to completion. “Come for me, angel.” Their eyes were locked as the entire world disappeared. 

It only took a moment for Cas to whimper and shove down onto Dean’s cock, spilling all over his stomach and chest. “Oh fuck, Dean.” He nearly yelled, sending Dean over as well. He moaned Cas’ name and slammed up into him, filling — hopefully the condom _—_ up with his release. 

Cas laid forward, kissing Dean in a way that let him know he was just as hooked as Dean was and then nuzzled his neck, as they caught their breath. 

_Crunch._

They both quickly glanced over at the door frame where Benny was shamelessly eating a bag of chips. “Oh, don’t mind me. Carry on.” He grinned and popped another chip in his mouth.

Dean blushed, “Shit, sorry man.” And he _almost_ was, Benny was the one that put this together.

“I’m not.” Cas smiled down at Dean and kissed him once, before climbing off and walking past Benny towards the bathroom. 

Dean couldn’t help but smile as he watched him leave. “You uh, want some help with that?” Dean pointed at Benny’s softening cock.

“Believe it or not, I actually came while watching you two. Can’t fake that passion brotha.” He walked over and offered Dean chips — which he took absentmindedly. 

_Passion…_

Like that didn’t just confuse Dean even more, cool.

**********

Afterwards was less awkward than Dean imagined it would be. They all cleaned up and dressed, then ate some cold pizza and had beers. They talked about the pride parade, which was also why Cas was in town, _should have talked more at the airport._ Dean thought to himself but then again, he’d felt that way for days.

Cas’ phone rang and he said goodbye, kissing them both — Dean a little longer _—_ before walking out the door. 

It wasn’t until Dean was climbing out of Benny’s truck that he realized he once again, forgot to ask Cas for his number. _Fuck!!_ Before he panicked, he used his damn brain. “Wait, Benny. Can I um…” he scratched his neck, “Get Cas’ number?”

Benny thought about it. “I would say no, because it isn’t mine to give. But I can without a single doubt in my mind, say he wouldn’t mind.” So he sent Dean over the contact information. “You’ll have to edit it from James to Cas, I haven’t had a chance to do that.”

“Will do, thanks Ben, that was… awesome.”

“That it was, until next time, Dean.” Dean closed his door and waved as he drove away.

This was decidedly the _craziest_ night of his life.


	2. Landing

**Summary for the Chapter:**

> Dean’s hooked! But does Cas feel the same…

* * *

“You gonna call?” Charlie asked, annoyingly chipper.

“Well, yeah… I don’t know what to say.” Dean admitted, sitting on her lime green couch with his phone in his hand.

“Just say _‘heya Cas. Wanna fuck? Maybe in a bed with just the two of us, this time?’”_ She mocked his deep voice. 

“I don’t sound like that!” 

_“I don’t sound like that!”_ She mocked again, making herself laugh even harder. “Okay, first of all, I’m funny, dude. Second of all, just be yourself. Ask him how long he’s in town for.” 

“Good opener!” He shrugged, she was annoying but Dean gave credit when deserved. 

He stared at Cas' contact information and paused, “Charlie, his phone is the same area code as mine!” _Shit! Cas was never on a layover in Kansas, he is_ from _Kansas._ He couldn’t fight his grin and began texting.

**Dean: Hey Cas, got your number from Benny, hope that’s ok. How long you in town for?**

He stared at it a moment before hitting send. 

“It’s fate!” Charlie made heart eyes and then sat next to him. “Did you really not look at his number this whole time?”

“What, it’s only been a day.” He blushed slightly 

“Yeah but you could have texted him allll of yesterday. Why did you wait until today? You _leave_ today” 

Dean scoffed, “No way? Had no idea.” He rolled his eyes, “Look, I don’t know what he’s looking for, Charles. I… what if he gets pissed I asked Ben for his phone number?”

“Doubt it. The sex was too good. Gross… but I’ve never seen you like that after a lay so it must have been great.” 

Dean had time to marinate on all of that, because Cas _didn’t_ text back. 

***********

Dean glances at his phone, “1pm and he hasn’t responded. Fuck, he thinks I’m a creep huh?” He began to pace.

“Chill. Maybe he’s just busy? He’s obviously into you, Dean.” Dean could tell she was just trying to make him feel better.

“If he was into me, he would have responded by now. My flight is in three hours.” 

Dean’s phone dinged. _Weird._

“See? The gods have heard your prayer.” She joked and walked over to read over his shoulder.

**Cas: Define “ok”? Because it is definitely okay that you have my number. But it isn’t okay that you took over a day to text me.**

Charlie bit back a smile and looked at Dean’s dumb red face. “Shit, Benny told him he gave it to me and then I didn’t text until the morning I’m leaving. He’s going to think I just want a quick fuck.” Dean groaned and set his phone down.

“I’d like the record to state that I told you to text yesterday.” Charlie held up her hand as if she was in court, earning herself an eye roll. 

_Ding_

**Cas: I’m joking, Dean. My brother read that message and said I sounded like a bitch. So, I’d like to clarify that, that was a joke. I’m in town until Thursday.**

Dean chuckled slightly, he could weirdly read these messages _in_ Cas’ voice already. He hesitated before deciding to just be honest.

**Dean: I was going to text yesterday but I couldn’t figure out what to say**

**Cas: Your text was sufficient enough. Did you get some help with it?**

**Dean: Yes, my lawyer looked over it prior**

**Cas: I happen to have a lawyer kink, can you give him my number too?**

Dean was grinning like an idiot.

**Dean: Sure, but I don’t think SHE is your type**

**Cas: You are correct.**

**Dean: Damn I should have texted yesterday, I’m leaving in about two hours**

**Cas: Yes. You should have.**

**Cas: However, I’ve come to the conclusion that you were NOT on a layover flight in Kansas. Maybe we could get together Friday back at home?**

**Dean: sounds good Cas**

Dean had to fight the small pang of disappointment in his gut. He really _didn’t_ want to wait until Friday. 

**Cas: Have a safe flight, Dean.**

**********

Dean was under no illusions that this date wouldn’t go well. They had the chemistry the sex was out of this world and they actually enjoyed talking to each other. To Dean’s surprise they texted a lot that week and even better, Cas initiated it.

**Cas: I’m watching a horrrrible movie with my brother and a condom just broke so naturally I thought of you.**

**Dean: I don’t know if I’m flattered or offended**

**Cas: You can be both.**

Dean sent back a shrugging emoji and Cas didn’t respond, but Cas opened that door and Dean wasn’t about to miss out on this one. The next day Dean texted first and the following day, Cas texted first, it brought Dean into the weekend feeling confident. 

Cas had got in the day before and just the mere thought of them being in the same town had Dean feeling butterflies. He still didn’t fully understand how Cas had turned him into a complete chick but for the first time in his life he wasn’t fighting it. 

Cas was awesome and Cas _knew_ he was awesome. Dean playing his normal games wasn’t an option because Cas was the _take no shit_ type and Dean could easily ruin a good thing. It wouldn’t be the first time.

Every time his phone made a sound, Dean ran to it, shoulders slumping when it was Sammy or Charlie. He loved talking to them, it just wasn’t what he wanted right now. Especially as he sat trying to figure out where to go on this date. 

Cas was from here. His whole damn life, just like Dean. He was sure Cas had done everything fun in this area so, how could he make this date different and stand out for Cas? 

The nerves really kicked in when he pulled up to Cas’ apartment. It was about ten minutes from his, _ten minutes._ How did they never once run into one another? The second he spotted Cas walking up, the mundane, dinner and a movie date was scratched except Cas was in sweatpants.

He approached the car and leaned into the window. “Are you coming inside?”

Dean hoped he didn’t look as confused as he felt. “Uh…”

Cas’ eyes widened. “Oh shit, you mean a _real_ date? Oops. Well I already prepped.”

“Just go get dressed, Cas. I’m trying to be a classy broad, here.”

Cas laughed beautifully and turned around. “Fine grouch, I’ll just grab a plug.”

The thought of Cas wearing a plug all night had Dean’s cock aching to be buried inside that perfect ass. _No. We’re going on a damn date,_ then _I will fuck the hell out of that sassy little shit._

He didn’t realize he was fidgeting until Cas came walking back out and froze, this time, he was wearing some nice dark blue jeans, a plain black shirt and a leather jacket. Nothing fancy but fuck, did he look good. He climbed inside like it wasn’t his first time getting in Baby and looked over at Dean with a smile. “Nice car.”

Dean grinned, “Thanks.” He pet the dashboard, “Her name is Baby. And she’s the best thing I own.” Dean turned on the car and put on some music.

“I beg to differ, that cock is the best thing to ever exist.” Cas pulled on his seatbelt, still wearing his cocky little smile.

“Yeah but that’s attached to me, so the actual nicest thing I own is _that_ ass.” _Two can play this game Cas._

He laughed fairly loudly before he responded, “I don’t know, you passed it up for this date so, maybe it isn’t as good.” Dean put the car back in park and turned to face Cas.

“Look, I want to fuck you right here right now, I’ve thought about you and that perfect ass every single day.” He paused and licked his lips. “But although we started this as just sex, I’d still like to actually get to know the person attached to that ass.”

Cas leaned in. “So, where are we going, casanova?”

Dean could have responded, but instead he kissed him. Cas instantly responded, a small whimper escaping his throat which egged Dean on, because he could feel he wasn’t the only one dying to skip everything and get right to the smut. He deepened the kiss for only a second before pulling away, leaving both of them breathless. 

“You look just as good dressed up as you did in sweatpants.” He whispered, placing his forehead against Cas’.

“Um… thanks. Even better naked.” He joked and Dean noticed his eyes were still closed. He was happy he wasn’t the only one affected here. 

“Trust me, Cas. I know.” Dean sighed and pulled away to put the car in drive and when he saw Cas adjust himself it was the icing on the cake.

Cas cleared his throat, “Is this some dinner and a movie date?”

Dean grinned, “Nah. That wouldn’t cut it now would it? We didn’t have a conventional start, can’t go on some conventional date.”

“Then where?” Dean stole a glance and could see Cas was actually excited. 

“Well isn’t it crazy we’re from here and have _never_ ran into each other?”

“Yes, actually. I’m sure it is because we hung out in different crowds, and then there’s the fact that I’m older than you, but it seems impossible we didn’t run into each other once in our whole lives. We probably did and just didn’t notice.” Cas was still watching him.

“I would have noticed. Have you seen you?” 

Cas laughed, “Yes, every day.” 

Dean shook his head, “I would have noticed those blue eyes anywhere, but how old are you? I thought we were the same age.”

Cas shrugged, “Twenty five. And I assumed you were like twenty one or something.”

“I’m twenty three, thank you very much.” 

“Excuse me.” He chuckled, “So, I graduated like two years before you. We definitely hung with different crowds.” 

They pulled up to Dean’s favorite diner and parked. “This is where the date ends.”

“Ends? Then why are we here?” Cas tilted his head, looking way too adorable for his own good.

Dean grinned and leaned in to kiss him again, “Sorry, couldn’t help it. Yes, _ends._ We’re walking the rest of it. I know this isn’t a _regular_ date, but you’re not a regular guy.”

“Is that a bad thing?”

“Not at all. It’s why I haven’t gone five minutes without thinking of you since we met.” Dean blushed after admitting that.

“I’ve thought about you too. Mostly that cock, but I like your other bits too.” He smiled cheekily.

“Cute.” Dean rolled his eyes fondly. “Then give me a chance to get you to like all my... bits. That came out weirder than I meant.”

Castiel laughed, “No, it was cute. Let’s go, show me your bits and then we’ll come back to Jo’s and have the best pie in the state.”

“Y-you like their pie?” 

“Do I have taste buds? Yes. Is that not okay?” Cas looked confused, not realizing that he just made Dean fall even more in love with him with the word pie.

“No. I mean, yes. Their pie is why we’re here. I come here whenever I can’t sleep and have their pie. 24/7 diner and they _always_ have fresh pie.” 

Cas eyed Dean with a small smile on his lips, “I’ve done the same thing. Not every time I can’t sleep, but sometimes. How did we never see each other?” 

“Dunno. It’s trippy right. I mean look,” Dean pointed at the wide open windows, “Imagine us sitting in different sections, facing opposite directions, completely clueless that such a good lay is right across the way.” He had to joke in the end, because the butterflies in his stomach were having babies. Did butterflies have babies? He’d probably google that later.

Cas was staring inside the diner, really imagining what Dean said and then turned to face him. “I’d probably have walked over like _‘Hey, can’t sleep either? Let me help with that in the bathroom._ ’” 

Dean laughed, “And I’d have been a fool to say no… is that really how you would have asked?”

Cas giggled a little and nodded. “I’m kind of a slut, if you haven’t noticed.

Dean frowned slightly. He did notice that, he just didn’t care. 

“Only when I’m single though, Dean. I have a high sex drive, but I’m also alone. I’ve been alone a long time. You asked if I was a phone sex opperator when we met, and I told you the truth. I am. Or, was. Now I just manage their website because it got really old really fast but because of that, I’ve worked from home for six years and even got my degree online. My people skills are rusty and being abrasive about what I want sexually is the only way I get laid, because no one wants the awkward guy. I’ll tone it down if it makes you uncomfortable.”

“No no. Don’t change who you are, I like who you are, but don’t think for one second people don’t want you. I see men _and_ women get completely thrown off when you look their way, you’re fucking gorgeous, Cas. I wasn’t upset you called yourself a slut, I don’t care about that. We fucked in an airport bathroom five minutes after we met, I’m in no place to judge. I just… want you to be _my_ slut.” He shrugged and pulled the keys out of the ignition.

“Like right now?” Cas asked, grinning and Dean scoffed. “I’m kidding. Later. Let’s go on a walk and hold hands like non-sluts do.” 

Dean shook his head and hid his smile as he climbed out of the car.

They walked until the sun began to set and discovered they hung out at all the same places as they strolled the downtown streets and made their way to the park. All the kids hung out here in highschool and it made Dean wonder what it would have been like if they were the same year. He definitely wouldn’t have had the balls to go for Cas, he was so deep in the closet back then he smelled like mothballs.

Dean definitely would have looked at Cas and probably would have jacked off while thinking of him, but that was as far as he had gotten with dudes back then. 

“Of all of this, where was your favorite place to go?” Dean asked, they were still holding hands proudly, even though they were sweaty and clammy but neither wanted to let go.

“Hands down, the water tower. They have a fence around it nowadays though.” He sighed, “Wish we could climb up there, I’d always wanted a hot guy to take me up there but I was a virgin in highschool so that definitely didn’t happen.”

“I know a way in, Cas. They put the fence up my senior year and we figured that shit out in like twenty minutes. Let’s go.” He tugged Cas’ hand excitedly and pulled him along. 

Cas has done everything with _some_ hot guy at some point in his adult life and if this was the _one_ sexual thing they can share between them and them alone, Dean was _not_ going to pass it up.

When they reached the top, they both looked down with flushed cheeks and lust blown eyes. Everything about this experience was arousing. They were in public, which was always hot and had wanted each other for hours, hell, days if you count the last week, and the tension was so thick it could be cut with a knife. Dean glanced down and saw Cas was just as hard as he was and pulled him in for a kiss, unable to wait anymore. When he kissed down Cas’ neck, he huffed a breathless laugh, “We’ve done enough foreplay to last the weekend. Will you fuck me now?” 

Dean reached down and gripped Cas’ ass. “Such a brat.” They made out while they worked on the other’s pants, clumsily and both shoved the pants and underwear down in one go. 

Cas wrapped his hand around their cocks and started frotting against him, moaning into his mouth. “Dean… I haven’t had anyone since that night at Benny’s and before that it was you at the airport. I’ve only wanted you.”

“Fuck Cas…” Dean rutted into Cas’ fist. “I only want you. Fuck, I don’t have a condom or lube.” 

“Shhh. I have both.” Cas pulled out two small packets of Astroglide. “Or I have two of one thing, shit. I should have been paying attention.”

“I have condoms in the car, or we can just...” Cas’ hand had slowed, but he was still stroking. 

“No, I need your cock inside of me in the next two minutes or I will jump off this water tower.” 

“Geez Cas, dramatic much?” He kissed him and continued, “We’ve technically already fucked raw.” Dean blushed and closed one eye nervously.

“That is correct.” Cas didn’t hesitate to open the lube and slick up their cocks. He turned and pulled out a plug, making Dean groan at the sight. 

“Fuck you’re beautiful, Cas.” Dean grabbed the packet and slicked Cas’ prepped hole, sliding two fingers inside with ease. 

“Dean… please… fuck me.”

It was so needy Dean’s knees nearly gave out and he pulled out his fingers and slid his cock inside. “Jesus!”

Cas huffed a laugh, “Castiel is fine.”

Dean slid out and slammed back inside, “I’ll just fuck the brat out of you then.”

Before Cas could speak, Dean began his pace. This wasn’t a place for a long session and he’d be lying if he said he wasn’t already close to the edge. Dean kissed along Cas’ neck and pumped his leaking cock as he fucked him.

Cas was a writhing mess but finally moved Dean’s hand onto his hip and began pumping himself, “Dean!” Was all the warning Dean had as Cas began to come and he held his breath so he could watch.

“Cas!” He called back and slammed inside, filling Cas up — this time on purpose. Dean kissed and sucked affectionately. “So good.”

Cas’ neck swiveled loosely against Dean’s shoulder, “Ssso good. So much better than I ever imagined it would be.” 

“Good. Don’t bring anyone else up here, Cas.”

Cas chuckled, “Then don’t disappear, Dean.” 

Dean didn’t miss the worry in Cas’ voice and all he wanted was to never hear that tone again, “I’m not going anywhere, Cas.”

Dean pulled out and put Cas’ plug back inside and the idea of his come inside of Cas’ while they do something as mundane as eat pie in a diner had his cock already twitching for more.

“Pie time?” Cas asked as he buckled his pants.

“Pie time. Then maybe…” Dean rubbed the back of his neck nervously, forgetting there was still lube on his hand. _Gross._ But he tried to play it off.

“Then maybe… you can come stay the night?” Cas offered and pulled out a wet wipe to clean Dean’s neck. 

“I mean..” Dean pulled Cas in again when he finished wiping the lube off. “I don’t really have plans this weekend.”

“I do.”

Dean’s face fell, “Oh, what are you doing?”

“You.” He grinned like he just made some deep intricate joke that Dean might not get.

“You’re ridiculous.” Dean couldn’t help but laugh and kiss those beautiful plump lips. “Let’s go.”

**Notes for the Chapter:**

> Hope you enjoyed the flight ✈️


End file.
